WO2015008296A1 - Free-flowing, solid, high active alkyl ether sulfates - Google Patents
Free-flowing, solid, high active alkyl ether sulfates Download PDFInfo
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- WO2015008296A1 WO2015008296A1 PCT/IN2014/000334 IN2014000334W WO2015008296A1 WO 2015008296 A1 WO2015008296 A1 WO 2015008296A1 IN 2014000334 W IN2014000334 W IN 2014000334W WO 2015008296 A1 WO2015008296 A1 WO 2015008296A1
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- Prior art keywords
- alkyl ether
- solid
- flowing
- free
- ether sulfates
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/08—Silicates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/10—Carbonates ; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
- C11D3/1246—Silicates, e.g. diatomaceous earth
- C11D3/128—Aluminium silicates, e.g. zeolites
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
Definitions
- the present invention relates to free-flowing, solid, high active alkyl ether sulfates. It particularly relates to free-flowing, solid alkyl ether 8 ⁇ 1 ⁇ 68 having active content of at least 50% by weight. It also relates to the process of manufacturing the free-flowing, solid, high active alkyl ether sulfates. In particular, it relates to the process of manufacturing the free-flowing, solid, high active alkyl ether sulfates at drying temperature of 80°C and above.
- the said alkyl ether sulfates are preferably used in laundry detergents and dish washing detergents.
- Detergent particles of high bulk density for example with a density of 600 g/1 or higher;
- the first type of process involves spray-drying an aqueous detergent slurry in a spray-drying tower to produce highly porous detergent granules (e.g., tower process for low density detergent compositions).
- the second type of process involves spray-drying an aqueous detergent slurry in a spray-drying tower as the first step, then, the resultant granules are agglomerated with a binder such as a nonionic or anionic surfactant, finally, various detergent components are dry mixed to, produce detergent granules (e.g., tower process plus non-tower [agglomeration] process for high density detergent compositions).
- the various detergent components are dry mixed after which they are agglomerated with a binder such as a nonionic or anionic surfactant, to produce high density detergent compositions (e.g., non- tower [agglomeration] process for high density detergent compositions).
- a binder such as a nonionic or anionic surfactant
- alkyl ether sulfates are the preferred and most widely used surfactant actives in compact laundry detergent compositions.
- Alkyl ether sulfates are known to be used in detergent compositions in aqueous solution or paste form. However as it is necessary to control the ratio of liquids to solids in order to form detergent granules, the maximum level of surfactant active material which may be incorporated in this manner is limited.
- alkyl ether sulfates are highly heat sensitive and therefore cannot be processed at elevated temperatures because of a tendency to decompose significantly at temperatures higher than 80°C. Therefore, they are not generally incorporated into spray-dried laundry powders via the slurry.
- alkyl ether sulfates are desirable to incorporate as a separate solid component to manufacture the compact laundry detergent compositions. Agglomeration is one such method wherein surfactant active material is dry mixed with other detergent components to prepare the solid detergent compositions. However, it has been still not possible to produce solid detergent compositions comprising high concentration of surfactant actives such as alkyl ether sulfates.
- Indian patent application no. 2623/MUM/2009 (Hindustan Unilever Ltd.) describes a free-flowing detergent granules comprising 10-30% of anionic surfactants.
- US 5,916,868 (Church & Dwight Co.) relates to a process for the production of a free- flowing high bulk density granular laundry detergent product comprising up to 40% of surfactant.
- EP 105 160 A discloses silicas loaded with aqueous surfactant solutions, preferably primary alcohol sulfate, alkyl ether sulfate or nonionic surfactant, for use in toothpastes; the highest surfactant loading disclosed in a free-flowing granule is 20 wt %, higher loadings being detrimental to flow.
- aqueous surfactant solutions preferably primary alcohol sulfate, alkyl ether sulfate or nonionic surfactant
- Another requirement for preparing compact detergent is to have high bulk density.
- Detergent compositions having a high bulk density are typically prepared by a process involving mixing or granulation of components of the composition and/or a base powder obtained for example from a spray-drying process and provide significant consumer benefits as compared to compositions of lower bulk density.
- anionic surfactant e.g. fatty alkyl ether sulfates
- a solid adjunct that is, a particle comprising the surfactant and other components of the composition e.g. sodium carbonate and a builder.
- anionic surfactant present in such adjuncts has been limited due to the need to provide good flow properties and to reduce the tendency to agglomerate.
- EP 430 603A discloses detergent granules containing at least 30 wt % anionic surfactant and a highly oil-absorbent filler, for example, a silica, in intimate contact with the anionic surfactant.
- EP 651 05 OA Patent & Gamble discloses detergent agglomerates comprising a solid, preferably water-soluble, a salt (for example, sodium silicate, carbonate or sulfate), and a fluid binder comprising an anionic surfactant (preferably alkyl ether sulfate) and sodium silicate.
- WO 97 10321 A discloses structured surfactant compositions comprising 35-60 wt % surfactant, preferably alkyl ether sulfate, 1-20 wt % hydrophilic finely-divided silica and 15-25 wt % moisture; these compositions are in the form of a "hardened continuous paste”.
- the inventors of the present invention have surprisingly found a unique process to produce free-flowing, solid, highly concentrated alkyl ether sulfates by processing it at temperature of above 80° C through unique combination of zeolites, carbonates, structurant and coating material. These solid, high active alkyl ether sulfates then can be used in combination with other detergent adjuvants to prepare the final detergent formulations or can be directly used as final detergent formulations.
- the present invention provides a process for manufacturing free-flowing, solid, high active alkyl ether sulfates by processing at temperature of 80° C and above. Accordingly, the present invention is directed to a process which produces free flowing, solid, high active alkyl ether sulfates involving the following steps:
- the present invention provides an efficient and economical process to facilitate large-scale production of free-flowing, solid, high active alkyl ether sulfates.
- the present invention provides free-flowing, solid, high active alkyl ether sulfates.
- the present invention provides free-flowing, solid alkyl ether sulfates with concentration of at least 50% by weight.
- the present invention provides free-flowing, solid alkyl ether sulfates with concentration of at least 60% by weight.
- the present invention provides free-flowing, solid alkyl ether sulfates with concentration of at least 70% by weight.
- the present invention provides free-flowing, solid, high active alkyl ether sulfates with coating.
- the present invention provides free flowing, solid, high active alkyl ether sulfates which comprises:
- Another aspect of the present invention provides free-flowing, solid, high active alkyl ether sulfates having very low moisture content of less than 5% by wt.
- the present invention provides free-flowing, solid, high active alkyl ether sulfates having needle and granule shapes.
- the present invention provides free-flowing, solid, high active alkyl ether sulfates with long storage and excellent transport efficiency without losing free flowability and with improved whiteness.
- the present invention provides colored, free-flowing, solid, high active alkyl ether sulfates.
- the present invention provides use of free flowing, solid, high active alkyl ether sulfates in laundry detergent compositions and dish-washing compositions.
- Figure I Graph of Dissolution time of 56% active Sodium lauryl ether sulfate (SLES) needles in 1% aqueous solution.
- SLES Sodium lauryl ether sulfate
- FIG II Graph of Dissolution time of 70% active Sodium lauryl ether sulfate (SLES) paste in 1% aqueous solution.
- SLES Sodium lauryl ether sulfate
- Figure III 67% active Sodium lauryl ether sulfate (SLES) needles.
- Figure IV 83% active Sodium lauryl ether sulfate (SLES) needles.
- Solid alkyl ether sulfates are prepared by mixing liquid alkyl ether sulfates with other ingredients and drying the mixture.
- alkyl ether sulfates being heat sensitive have never been able to process at more than 80°C and hence it takes many hours to prepare solid, high active alkyl ether sulfates through drying.
- inventors of the present invention have found out a process for preparing solid, high active alkyl ether sulfates which can be carried out by drying at temperatures higher than 80°C without degradation of alkyl ether sulfates.
- the inventors of the present invention have found that the unique combination of zeolite ' s and carbonates gives excellent buffering towards H + ions and helps to achieve the high active alkyl ether sulfates with reduced batch cycle time.
- Alkyl ether sulfates are highly heat sensitive and can be hydrolyzed in presence of heat (temperature more than 80°C) and moisture. Hydrolysis product gives sulfuric acid and ethoxylated alkyl alcohol and acidic pH of the material catalyses hydrolysis further. Addition of zeolite and carbonate, in combination, during drying stage, arrests hydrolysis of alkyl ether sulfates remarkably and hence alkyl ether sulfates withstand high drying temperature for prolonged hours.
- alkyl ether sulfates that can be prepared as per present invention are agglomerates, powder, extrudates, flakes, beads, noodles and preferably needles and granules.
- the present invention is directed to a process for preparing free flowing, solid, high active alkyl ether sulfates involving the following steps:
- step (ii) adding amorphous zeolite, carbonate and structurant to step (i) to form a mixture;
- the present invention further provides a free flowing, solid, high active, alkyl ether sulfates comprising
- the moisture content of free- flowing, solid, high active alkyl ether sulfates of the present invention is preferably between 0 to 10 wt%, more preferably between 0 to 5 wt%, from the viewpoint of caking resistance. Lesser the moisture content, lesser is the ⁇ caking and higher is the free- flowability.
- the pH maintained during the process is between 9-14.
- Alkyl ether sulfates are generally defined as salts of sulfated adducts of ethylene oxide with alkyl alcohols containing from about 8 to about 22 carbon atoms, which preferably correspond to formula: RO— (CH 2 CH 2 0)nS0 3 X
- R is a linear or branched hydrocarbon radical containing 8 to 22 carbon atoms
- n is an average number of ethylene oxide (EO) moles between 0.5 to 3.
- X is an alkali metal, alkaline earth metal, ammonium or substituted ammonium.
- the alkyl ether sulfates of the present invention have a alkyl chain containing 8 to 22 carbon atoms, preferably, the fatty alkyl chain contains 8 to 18 carbon atoms, preferably 12 to 18 carbon atoms, more preferably 12 to 16 carbon atoms, and still more preferably 12 to 14 carbon atoms.
- Typical examples of alkyl chain include, caprylyl, capryl, lauryl, myristyl, cetyl, palmityl, stearyl, behenyl, and the technical mixtures thereof obtained.
- Preferred examples are lauryl, coco, and mixture of lauryl and myristyl alkyl chain.
- the average degree of ethoxylation present in the alkyl ether sulfates of the present invention is from about 0.5 to 10 moles of ethylene oxide, preferably about 0.5 to 3 moles of ethylene oxide.
- a particularly preferred alkyl ether sulfate for use in the present invention is C 12 - i4 alkyl ether sulfate having average 1 mole of ethylene oxide, commercially available under the trade name "Galaxy LES 170" and another one is C 12 - 14 alkyl ether sulfate having average 2 moles of ethylene oxide, commercially available under the trade name "Galaxy LES 70" and still another one is C 12 - j 4 alkyl ether sulfate having average 0.5 moles of ethylene oxide.”
- alkyl ether sulfates are commonly available as 28% aqueous solution and 70% aqueous paste. Other concentrations can always be prepared with the known art, and used for the present invention. These alkyl ether sulfates also contain unsulfated ethoxylated fatty alcohols as an impurity in an amount of up to 3 wt% and inorganic salts such as sodium chloride and sulfates up to 2% by weight.
- Zeolites are known for assisting or enhancing cleaning performance and controlling mineral hardness. Zeolites are of great importance in most currently marketed heavy duty granular detergent compositions, and can also be a significant builder ingredient in solid detergent formulations.
- the zeolites may be crystalline or amorphous in structure and can be naturally occurring aluminosilicates or synthetically derived. Crystalline zeolites can be commercially available such as zeolite A (zeolite 4 A), maximum aluminium zeolite P (zeolite MAP), zeolite B, zeolite X, zeolite Y.
- amorphous zeolite used is "DET BUILD - 150" supplied by Bengal Multi Gas Base Chemicals Pvt. Ltd. It contains minimum 15.6% Na 2 0, 32.3% Si0 2 , 29.0% A1 2 0 3 . It has water adsorption capacity of about 24%.
- the crystalline zeolite used in the present invention is "sodium alumino silicate zeolite 4A" supplied by Zeolites And Allied Products Pvt. Ltd. It contains minimum 18.0% Na 2 0, 38.0% Si0 2 , 34.0% A1 2 0 3 . It has water adsorption capacity of about 24%.
- the inventors of the present invention have found that the amorphous and crystalline zeolites play an important role for getting the desired solid form, particularly the ratio of amorphous to crystalline zeolites.
- the ratio of amorphous zeolite to crystalline zeolite should be from 80:20 to 20:80.
- Another aspect of the present invention is the sequence of addition of both types of zeolites.
- Amorphous zeolite is added in the first step of the heating whereas addition of crystalline zeolite is done just before last step of coating of solid alkyl ether sulfates. If crystalline zeolite is added at the initial stage, it results in stickiness of the finally formed product.
- the free-flowing, solid, high active alkyl ether sulfates comprise 5-50 wt% zeolites, preferably 5-40 wt% zeolites.
- Laundry detergent compositions comprising a water-soluble alkaline carbonates are well- known in the art.
- Such builders improve the cleaning power of the detergent composition, for instance, by the sequestration or precipitation of hardness causing metal ions such as calcium, peptization of soil agglomerates, reduction of the critical micelle concentration, and neutralization of acid soil, as well as by enhancing various properties of the active detergent, such as its stabilization of solid soil suspensions, solubilization of water-insoluble materials, emulsification of soil particles, and foaming and sudsing characteristics.
- carbonates suitable for the present invention include alkaline earth metal carbonates such as magnesium carbonate, calcium carbonate and alkali metal carbonates such as sodium carbonate, potassium carbonate, preferably sodium carbonate.
- the present invention may include the biearbonates of the alkaline earth metals and alkali metals.
- the product of the present invention contains sodium carbonate in order to increase detergency and easy processing.
- Sodium carbonate may suitably be present in amounts ranging from 0.5 to 5 wt %, preferably from 0.5 to 2 wt %.
- the ratio of carbonate to Zeolite is 1 : 10 to 1 :50.
- Suitable structurant may include materials selected from soaps, sugars, water-soluble polymers, alkali metal silicates and combinations thereof.
- Preferred examples include glucose, maltose, sucrose, ethylene glycol, homo- and copolymers, polyvinyl alcohols polyacrylates, and acrylic/maleic copolymers (eg Sokalan (Trade Mark) CP5 ex BASF).
- sugar as used herein is a generic term for a class of carbohydrates which are usually crystalline and sweet by nature, and which are water soluble. Sugars are formed from glucose and fructose units which are sugars in their own right. Preferred sugars include glucose, fructose, galactose, sucrose, maltose, lactose, sorbitol, manitol, rafinose, and trehalose.
- sucrose which is most preferred for reasons of availability and cheapness
- glucose fructose
- maltose malt sugar
- cellulose lactose which are disaccharides.
- 0.5-3 wt % sugar is used, preferably 2 wt %.
- the solid alkyl ether sulfates of the present invention can be colored with various color pigments without affecting its physical performance. These solid alkyl ether sulfates are mixed with color in mixer or blender and then extruded or converted into desired form.
- Color Pigments may be selected from inorganic and organic pigments; preferably the pigments are organic pigments.
- the pigment may be of any color; preferably the pigment is blue, red, pink or yellow in color.
- Preferred pigments are CC Blue Fine Paste 615 (Clariant Chemicals), Liquitint Red SP (Milliken Chemicals), Liquitint Yellow LP (Milliken Chemicals).
- Blue pigment is in paste form and need to be diluted with water before coloring and red and yellow are in liquid form and are used as it is. Pigments are preferably present from 0.1 to 0.8 wt%.
- the solid alkyl ether sulfates of the present invention are coated with a coating material.
- the coating material is silicates, preferably silica. Coating is applied as a final step by using dry powder of the coating material. Due to this coating, the solid alkyl ether sulfates becomes non-sticky and free-flowable.
- the particle coating layer imparts new surface and appearance properties on solid alkyl ether sulfates. Further, the coated solid alkyl ether sulfates provide improved flowability profile to the final detergent products also without any clumping.
- coating is done by "MFIL-100 precipitated silica” supplied by Madhu Silica Pvt. Ltd. It has minimum 98.5% Si0 2 content.
- Titanium dioxide can be added optionally for improving the whiteness of the solid alkyl ether sulfates. About 0.01 -1 wt. % of titanium dioxide can be added.
- the solid Alkyl ether sulfates of the desired form can be prepared by known conventional methods such as
- the free-flowing, solid, high active alkyl ether sulfates prepared by the processes claimed herein may be used directly as final detergent compositions or they may be mixed with other detergent ingredients or additives to make final detergent compositions for laundering fabrics and the dish-washing purposes.
- solid alkyl ethers sulfates of the present invention are so excellent in free- flowability that it retains its flowability even if we stack and store it for longer time or longer days. This property will help in transportation as it will make the transport of the material without having formation of clumps or agglomerates during transportation.
- Example 3 was repeated but without adding amorphous zeolite and Sodium carbonate. It was observed that SLES was getting hydrolyzed substantially and the active content decreased in the range of 8-10 % within 4 hours of heating at reaction temperature of 90- 100° C.
- Example 3 was repeated without adding amorphous zeolite. It was observed that SLES was getting hydrolyzed and the active content decreased by 8-9% in 4 hours of heating at reaction temperature of 90- 100 °C.
- Example 3 was repeated without addition of sodium carbonate. It was observed that the active content decreased by 6-8 % within 4 hours of heating at 90-100 °C. It was found that after 100 C, material starts hydrolyzing fast and when the temperature reached 106 C, entire SLES got hydrolyzed.
- Dissolution test was conducted by dissolving 1 gm of sample in 100 ml distilled water and change in millivolts was recorded. At constant millivolts, it was concluded that dissolution is complete.
- Dissolution time of 56% active Sodium lauryl ether sulfate (SLES) needles in 1% aqueous solution is illustrated in Figure-I whereas dissolution time of paste of 70% active Sodium lauryl ether sulfate (SLES) in 1% aqueous solution is illustrated in Figure II.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/905,423 US10287531B2 (en) | 2013-07-18 | 2014-05-19 | Free-flowing, solid, high active alkyl ether sulfates |
EP14825618.3A EP3022279B1 (en) | 2013-07-18 | 2014-05-19 | Free-flowing, solid, high active alkyl ether sulfates |
ES14825618T ES2718092T3 (es) | 2013-07-18 | 2014-05-19 | Alquil éter sulfatos sólidos altamente activos que fluyen libremente |
RU2015151172A RU2634690C2 (ru) | 2013-07-18 | 2014-05-19 | Сыпучие твердые высокоактивные алкилэфирсульфаты |
JP2016526754A JP2016530359A (ja) | 2013-07-18 | 2014-05-19 | 自由流動性固体状高活性アルキルエーテル硫酸塩 |
BR112015026833A BR112015026833A2 (pt) | 2013-07-18 | 2014-05-19 | processo para preparar sulfatos de éteres de alquilas muito ativos, sólidos, de fluxo livre, composições de sulfato de éter de alquila muito ativo, sólidas, de fluxo livre, composição detergente para lavar roupa, composição detergente para lavar louça e uso das composições de sulfato de éter de alquila muito ativo, sólidas, de fluxo livre |
CN201480024727.1A CN105378047A (zh) | 2013-07-18 | 2014-05-19 | 自由流动的固体高活性烷基醚硫酸盐 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN2404/MUM/2013 | 2013-07-18 | ||
IN2404MU2013 IN2013MU02404A (pt) | 2013-07-18 | 2014-05-19 |
Publications (1)
Publication Number | Publication Date |
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WO2015008296A1 true WO2015008296A1 (en) | 2015-01-22 |
Family
ID=52345811
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/IN2014/000334 WO2015008296A1 (en) | 2013-07-18 | 2014-05-19 | Free-flowing, solid, high active alkyl ether sulfates |
Country Status (9)
Country | Link |
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US (1) | US10287531B2 (pt) |
EP (1) | EP3022279B1 (pt) |
JP (1) | JP2016530359A (pt) |
CN (1) | CN105378047A (pt) |
BR (1) | BR112015026833A2 (pt) |
ES (1) | ES2718092T3 (pt) |
IN (1) | IN2013MU02404A (pt) |
RU (1) | RU2634690C2 (pt) |
WO (1) | WO2015008296A1 (pt) |
Citations (8)
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WO1997010321A1 (en) * | 1995-09-12 | 1997-03-20 | The Procter & Gamble Company | Compositions comprising hydrophilic silica particulates |
WO1997032002A1 (en) * | 1996-02-26 | 1997-09-04 | Unilever Plc | Production of anionic detergent particles |
US5807187A (en) * | 1995-10-24 | 1998-09-15 | Longball Sports | Air channeling golf club head |
WO1998054278A1 (en) * | 1997-05-30 | 1998-12-03 | Unilever Plc | Detergent compositions |
WO1998054289A1 (en) * | 1997-05-30 | 1998-12-03 | Unilever Plc | Free-flowing particulate detergent compositions |
WO2000031233A1 (en) * | 1998-11-20 | 2000-06-02 | Unilever Plc | Particulate laundry detergent compositions containing anionic surfactant granules |
WO2000031223A1 (en) * | 1998-11-20 | 2000-06-02 | Unilever Plc | Granular detergent components and particulate detergent compositions containing them |
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DE3236180A1 (de) | 1982-09-30 | 1984-04-05 | Akzo Gmbh, 5600 Wuppertal | Mit tensid beladene kieselsaeure, verfahren zu deren herstellung und deren verwendung |
JPH0732320B2 (ja) * | 1988-04-28 | 1995-04-10 | 茂一 渋谷 | 反射板のある電波暗室 |
GB8926644D0 (en) | 1989-11-24 | 1990-01-17 | Unilever Plc | Detergent composition |
EP0651050A1 (en) | 1993-11-03 | 1995-05-03 | The Procter & Gamble Company | Surfactant agglomerate particle |
PT663439E (pt) * | 1994-01-17 | 2000-12-29 | Procter & Gamble | Processo para a preparacao de granulos de detergente |
WO1995034625A1 (en) * | 1994-06-13 | 1995-12-21 | The Procter & Gamble Company | Detergent composition containing anionic surfactants and water-soluble saccharides |
JP2936220B2 (ja) * | 1994-08-12 | 1999-08-23 | 花王株式会社 | ノニオン洗剤粒子の製造方法 |
GB9618875D0 (en) * | 1996-09-10 | 1996-10-23 | Unilever Plc | Process for preparing high bulk density detergent compositions |
US5807817A (en) * | 1996-10-15 | 1998-09-15 | Church & Dwight Co., Inc. | Free-flowing high bulk density granular detergent product |
JP2929276B2 (ja) * | 1996-12-18 | 1999-08-03 | 花王株式会社 | ノニオン洗剤粒子の製造方法 |
JP2005120160A (ja) * | 2003-10-14 | 2005-05-12 | Kao Corp | 粉末洗浄剤組成物 |
JP2005239809A (ja) * | 2004-02-25 | 2005-09-08 | Kao Corp | 自動食器洗浄機用洗剤組成物 |
CN101160382A (zh) * | 2005-02-18 | 2008-04-09 | 荷兰联合利华有限公司 | 洗涤剂组合物 |
JP5225545B2 (ja) * | 2005-12-21 | 2013-07-03 | ライオン株式会社 | 粒状洗浄剤組成物 |
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2014
- 2014-05-19 EP EP14825618.3A patent/EP3022279B1/en not_active Not-in-force
- 2014-05-19 BR BR112015026833A patent/BR112015026833A2/pt not_active IP Right Cessation
- 2014-05-19 WO PCT/IN2014/000334 patent/WO2015008296A1/en active Application Filing
- 2014-05-19 CN CN201480024727.1A patent/CN105378047A/zh active Pending
- 2014-05-19 RU RU2015151172A patent/RU2634690C2/ru not_active IP Right Cessation
- 2014-05-19 IN IN2404MU2013 patent/IN2013MU02404A/en unknown
- 2014-05-19 JP JP2016526754A patent/JP2016530359A/ja active Pending
- 2014-05-19 US US14/905,423 patent/US10287531B2/en active Active
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WO1997010321A1 (en) * | 1995-09-12 | 1997-03-20 | The Procter & Gamble Company | Compositions comprising hydrophilic silica particulates |
US5807187A (en) * | 1995-10-24 | 1998-09-15 | Longball Sports | Air channeling golf club head |
WO1997032002A1 (en) * | 1996-02-26 | 1997-09-04 | Unilever Plc | Production of anionic detergent particles |
WO1998054278A1 (en) * | 1997-05-30 | 1998-12-03 | Unilever Plc | Detergent compositions |
WO1998054289A1 (en) * | 1997-05-30 | 1998-12-03 | Unilever Plc | Free-flowing particulate detergent compositions |
WO2000031233A1 (en) * | 1998-11-20 | 2000-06-02 | Unilever Plc | Particulate laundry detergent compositions containing anionic surfactant granules |
WO2000031223A1 (en) * | 1998-11-20 | 2000-06-02 | Unilever Plc | Granular detergent components and particulate detergent compositions containing them |
WO2001081528A1 (en) * | 2000-04-20 | 2001-11-01 | Unilever Plc | Granular detergent component and process for its preparation |
Also Published As
Publication number | Publication date |
---|---|
US20160168512A1 (en) | 2016-06-16 |
RU2015151172A (ru) | 2017-06-02 |
CN105378047A (zh) | 2016-03-02 |
EP3022279A1 (en) | 2016-05-25 |
ES2718092T3 (es) | 2019-06-27 |
JP2016530359A (ja) | 2016-09-29 |
IN2013MU02404A (pt) | 2015-06-19 |
BR112015026833A2 (pt) | 2017-07-25 |
EP3022279B1 (en) | 2019-03-27 |
EP3022279A4 (en) | 2017-03-22 |
US10287531B2 (en) | 2019-05-14 |
RU2634690C2 (ru) | 2017-11-03 |
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